Synthesis of Streptovitacin-C2 Isomers

概要

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(2R*, 4S*, 6S*, αS*)- and (2R, 4R, 6R, αS)-Streptovitacin-C2 (STV-C2) (1a and 1b) were synthesized by an aldol condensation of (2R*, 4S*)- or (2R, 4R)-2, 4-dimethyl-2-trimethylsiloxy-1-cyclohexanone (15a or 15b) with 4-(2-oxoethyi)-2, 6-piperidinedione (16), which was followed by desilylation of the products. The stereochemistry of the synthesized STV-C2 isomers (1a and 1b) was elucidated by NMR. STV-C2 isomers (1a and 1b) did not show strong antimicrobial activity against Saccharomyces cerevisiae and Pyricularia oryzae.